What Trainer
For the second plane, its hard to beat the Sig Four-Star 40. Its able to be trimmed to fly as stable as the trainer (it comes with a begginner's guide... it makes a good trainer with the CG 1/2 inch ahead of the spar) It can also be trimmed to do a lot of aerobatics. Construction is veryquick and easy. (the running joke is... open box, dump in glue, shake well, completed plane falls out.)
Handling planes in wind... try to do take-off and landing directly int the wind if possible. If you have a cross-wind, apply SLIGHT aileron into the wind, and be ready to correct EITHER direction with rudder. This works whether using a high wing or a low wing model. Note that if the wind is from the left, you'll have more trouble with take-off than if the wind is from the right. The torque of the engine helps a bit when taking off with the crosswind from the right.
The "weathervaning" effect is worst when the plane is just about to lift off. You need to be ready to level the plane quickly when t gets off the ground. When it begins to drift with the wind instead of weathervaning (its an effect of having the wheels on the ground) the correction input you've been giving wll suddenly be too much.